1. Field of the Invention
The present invention relates to a novel method of producing a vinyl phosphine oxide having high optical activity, which is useful as a material for producing optically active compounds.
2. Description of the Prior Art
Recently, the ratio of the optically active medicine of all the medicine in the market is increasing year after year. In the last five years, the optically active medicine amounted to 39% of the share. Moreover, the need for optically active substances is not limited to the field of medicine, but extends to fields such as agricultural chemicals, perfume, sweetener, seasoning, and even high-performance materials such as ferroelectric liquid crystal and packings for high performance liquid chromatography.
Being a functional group having high reactivity, the vinyl bonding is known to be especially useful as a building block in producing novel optically active compound having its asymmetric center on a phosphorus atom (K. M. Pietrusiewicz, M. Zablocka, and W. Wiesniewski, Phosphorus, Sulfur, and Silicon, 1990, 49/50, 263-266).
As a conventional method of producing an optically active vinyl phosphine oxide, a method is proposed, for example, as shown in the general formula mentioned below; ##STR3## wherein phenyldichlorophosphane is reacted with butanol under the presence of triethylamine, and then Grignard reaction is performed using vinylmagnesium bromide. Next, the product is reacted with (-)-menthyl bromoacetate ester, recrystallized using benzene so as to fractionally crystallize the optically active substance, in order to obtain an optically active (-)-(mentoxy carbonylmethyl)phenyl vinyl phosphine oxide. Then, the result is subjected to reflux in dimethyl sulfoxide hydrate under the presence of lithium chloride at the temperature of 180.degree. C. for two hours, so as to obtain the subject (-)-methyl phenyl vinyl phosphine oxide {(Ryszard Bodalski, Ewa rutkowska-Olma, Tetrahedron, 36, 2353-2355), (K. Michal Pietrusiewicz, Maria Zablocka, and Jaroslaw Monkiewicz, J. Org. Chem., 1984, 49, 1522-1526)}.
Also, as a method of producing optically active vinyl phosphine oxide having extremely high optical purity, Japanese Laid-Open Patent Publication No. S64-75495 discloses a method of contacting a racemic modification of a phosphine oxide class shown by the following general formula (3): ##STR4## (in the formula, Ar represents an aryl group, R.sup.1 and R.sup.2 are a low-rank hydrocarbon group with 1-6 carbons which are dissimilar, with an example of vinyl group shown) to a 2,2-dihydroxy-1,1-binaphthyl in an organic solvent, and then separating and dividing the produced inclusion complex.
Also, the present inventors proposed in Japanese Patent Application No. H10-29803 a method of producing an optically active phosphine oxide carboxylic acid, wherein an optically active 1-phenyethylamine is reacted with a phosphine oxide carboxylic acid of a racemic modification shown by the following general formula (4): ##STR5## (in the formula, R.sup.1 and R.sup.2 represent a linear or branched alkyl group with 1-18 carbons, or a substituted or non-substituted phenyl group, and A represents an alkylene group, wherein R.sup.1 and R.sup.2 are of dissimilar groups), and a produced diastereomeric salt is separated using the difference in solubility against a solvent which is subsequently decomposed by acid, so as to obtain an optically active phosphine oxide carboxylic acid.